6-bromo-2-(4-methoxyphenyl)benzo[d]thiazole | 154558-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-bromo-2-(4-methoxyphenyl)benzo[d]thiazole
• 英文别名: 6-Bromo-2-(4-methoxy-phenyl)-benzothiazole；6-bromo-2-(4-methoxyphenyl)-1,3-benzothiazole
• CAS: 154558-92-6
• 化学式: C₁₄H₁₀BrNOS
• 分子量: 320.209
• InChiKey: QUYOAICKVDROPI-UHFFFAOYSA-N

物化性质

• 沸点：
  440.0±51.0 °C(Predicted)
• 密度：
  1.512±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-2-(4-methoxyphenyl)benzo[d]thiazole 在 氮气 、 乙酸乙酯 、 盐酸 、 Brine 、 正己烷 作用下， 以 三溴化硼 、 Brine 为溶剂， 反应 18.0h， 以yielding the title compound (115 mg, 100%) as a tan solid的产率得到6-bromo-2-(4-hydroxyphenyl)benzothiazole
  参考文献：
  名称：

  ER-beta-selective ligands

  摘要：

  本文描述了化学式（I）的化合物，用作雌激素受体-β选择性配体，其中X为O或S；R1，R3-R6如规范所述。描述了在治疗阿尔茨海默病，焦虑症，抑郁症，骨质疏松症，心血管疾病，类风湿性关节炎和前列腺癌方面使用这些化合物的方法，以及制造它们的过程。

  公开号：

  US20070208066A1
• 作为产物：
  描述：

  N-(4-溴苯基)-4-甲氧基苯甲酰胺 在 劳森试剂 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 氯苯 为溶剂， 反应 3.0h， 生成 6-bromo-2-(4-methoxyphenyl)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors

  摘要：

  Protein tyrosine kinases occupy a central position in the control of cellular proliferation and its inactivation might lead to the discovery of a new generation anticancer compounds. Substituted benzothiazoles have been found to mimic the ATP-competitive binding of genistein and quercetin to tyrosine kinase. A series of novel 2-phenyl-1,3-benzothiazoles were synthesized and characterised by IR, H-1 NMR and mass spectroscopy. All the compounds were tested for their anticancer activity against MCF-7 breast cancer cell line with the MTT assay. Most of the compounds showed moderate to good anti-breast cancer activity. Anticancer activity varied with substitution on the benzothiazole nucleus with halogens and at 4 position, substitution of the 2-phenyl moiety with methyl and methoxy groups was also explored. Among the compounds tested with MTT assay, mono fluoro substitution on benzothiazole nucleus and 4'-methyl variations at 2-phenyl position demonstrated highest percent growth inhibition of MCF-7 cells. Docking studies of the synthesised compounds was done on EGFR using GRIP batch docking method to study their observed activity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmgm.2010.04.003

文献信息

• Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
  作者：Amrita Dey、Alakananda Hajra

  DOI：10.1021/acs.orglett.9b00245

  日期：2019.3.15

  A highly efficient method for the synthesis of 2-arylbenzothiazoles has been developed using readily available aromatic amines, benzaldehydes, and NH4SCN as a sulfur source. A library of 2-arylbenzothiazoles with wide functional group compatibility has been synthesized in good yields through iodine-mediated oxidative annulation.

  已经开发了一种高效的合成2-芳基苯并噻唑的方法，该方法使用容易获得的芳族胺，苯甲醛和NH 4 SCN作为硫源。通过碘介导的氧化环化反应，以高收率合成了具有广泛官能团相容性的2-芳基苯并噻唑文库。
• Therapeutic compounds
  申请人：——

  公开号：US20040102435A1

  公开（公告）日：2004-05-27

  Compounds of the formula (I) for use as an estrogen receptor-&bgr;-selective ligand are described wherein: X is O or S; and R 1 , R 3 R 6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  描述了用作雌激素受体β选择性配体的化合物的公式(I)，其中：X为O或S；R1，R3和R6如规范中所述。描述了这些化合物在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌中的用途；以及制备它们的过程。
• ER-B-SELECTIVE LIGANDS
  申请人：Bernstein Peter

  公开号：US20060106074A1

  公开（公告）日：2006-05-18

  The invention relates to novel compounds having the general formula: (1) wherein X is O or S which are useful as selective ER-β ligands in the treatment or prophylaxis of Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis or prostate cancer.

  本发明涉及具有以下一般式的新化合物：（1），其中X为O或S，这些化合物在治疗或预防阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎或前列腺癌中作为选择性ER-β配体具有用途。
• Therapeutic benzothiazole compounds
  申请人：Barlaam Bernard

  公开号：US20060111408A1

  公开（公告）日：2006-05-25

  Compounds of the formula (I) for use as an estrogen receptor -β-selective ligand are described wherein: X is O or S; and R 1 , R 3 -R 6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  本文描述了化学式（I）的化合物，可用作雌激素受体-β选择性配体，其中X为O或S；R1、R3-R6如规范中所述。描述了在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌方面使用这些化合物的方法，以及制备它们的过程。
• Therapeutic benzoxazole compounds
  申请人：AstraZeneca AB

  公开号：US07045539B2

  公开（公告）日：2006-05-16

  Compounds of the formula (I) for use as an estrogen receptor-β-selective ligand are described wherein: X is O or S; and R1, R3 R6 are as described in the specification. The use of these compounds in treating Alzheimer's disease, anxiety disorders, depressive disorders, osteoporosis, cardiovascular disease, rheumatoid arthritis and prostate cancer is described; as are processes for making them.

  本发明描述了化学式（I）的化合物，用作雌激素受体-β选择性配体，其中：X为O或S；R1、R3、R6如说明书中所述。本发明还描述了这些化合物在治疗阿尔茨海默病、焦虑症、抑郁症、骨质疏松症、心血管疾病、类风湿性关节炎和前列腺癌中的应用，以及制备它们的过程。